I won't try and convince people that hose extenders are better than longer valves. I know that once you have a part fail to perform as expected many will consider the item fundamentally defective. Same goes for long stem valves or short "Alligator" extenders.
However I have used this set-up since 3/08 with zero problems
You will note the hose end is firmly attached so there is no movement of the hose. When I check inflation I hold the hose with my other hand to prevent over-stressing the hose mount.
Oh yes I do have TPMS but mine are internal mount type.
I will point out that just as tires can "age out" before they wear-out all rubber components have a finite life. You have seen this with things like rubber bands and windshield wiper blades.
Replacing the rubber parts of your bolt in metal stems whenever you buy new tires is a suggestion I have been making for years and you may have noticed that this is standard practice at good tire shops.
Other components to consider are valve caps. You should not be using the soft plastic caps in high pressure applications. caps serve 2 purposes First to keep dirt out of the valve core and second to help keep air in if the core leaks. Metal caps have rubber "o-rings: gaskets that age and can lose their ability to seal.
Here is a vlave core leak
and here is the size of the grit that was causing this leak
The use of "Alligator" cap/extenders may not prevent dirt from entering the valve core body.
Valve body rubber parts that seal the valve to the wheel should be replaced too.
Use long stems or extenders or hoses as you wish but do not simply jab the gauge on the end.
Use Alligator extenders or metal caps but be sure to clean off then end of the Alligator caps so you don't blow dirt into the valve.
Replace rubber components whenever you replace tires, or sooner if you wish.
ALWAYS use some type of cap to keep dirt out and remember that metal caps w/O-Rings can help keep air in if the valve core develops a leak
Use a TPMS as if you develop a leak it should warn you as soon as you loose 10% to 15% of the hot air pressure.
I have a number of posts with "Valve
" as the tag if you want more info.